During the Separatist Crisis, Dooku had her infiltrate the undercover spy ring Vos was establishing for Tholme in the guise of a prostitute. To gain Quinlan's confidence, she was to pretend to love him, but as she fell in love with him legitimately, she stopped working for Dooku and became Quinlan's agent.

On the Wheel, shortly after the Battle of Geonosis, under direction of another of Dooku's agents, Tookarti, Hentz stole a data chip from the crime lord Zenex, containing the Confederacy of Independent Systems plans to attack Kamino. Zenex ordered the mercenary Grakko to find and kill her, but Grakko didn't succeed—Hentz killed him instead, by setting off one of his own thermal detonators. However, she soon ended up in a garbage pit—within it was a dianoga. She was barely saved by Vos and his former apprentice, Aayla Secura, posing as a mechanic named Jayzaa. She overheard their conversation about the disc and guessed that they were Jedi. In order to ensure that the Galactic Republic would be able to successfully defend Kamino, she was to give the data chip back to Zenex, under the watchful eye of Jedi Knights Vos and Aayla Secura. The plan appeared to be going well: Zenex promised he wouldn't kill her if she handed over the disc. Instead, he used his Falleen pheromones to make her point a blaster at her own head and kill herself. Vos intervened and saved Hentz's life, whereas Secura killed Zenex by impaling him on her lightsaber.

Vos escapes with Hentz's help.

Hentz and Vos eventually fell in love, despite the protestations of Vos' Padawan Aayla and the disapproval of Vos' former master Tholme. During Vos' arrest and defection in the aftermath of the Battle of Brentaal IV, Hentz took a speeder and helped him escape, knowing full well that she would do jail time again. Weeks later, Vos managed to infiltrate Dooku's inner circle, and Tholme released Hentz so she could serve as a go-between for Vos and himself.

While Vos continued his role as a double agent, Hentz was with him. She traveled with him to Coruscant during his quest to find and destroy the person he thought was the second Sith. After Vos killed SenatorViento under the false impression that he was the second Sith, Hentz was to pick him up after he fled the building, but was stopped by Dooku's Dark AcolyteTol Skorr.

Hentz was soon forced to come with Vos to Viento's tomb, where he read his carbonite corpse. As part of Vos' further quest, Dexter Jettster put out the word that Hentz wanted to hire the Anzatibounty hunterSaljé Tasha for a job. When Vos met Tasha, he confronted the bounty hunter and managed to draw the memories he sought from her mind. When her Anzati proboscises uncurled as she tried to feed upon his mind, Hentz interfered and hit her hard with a metal pole. Deciding that Tasha served her purpose, she decided to kill the Anzat. Tasha, angry that she had barely tasted the richness of Quinlan's mind, vowed vengeance on her.

Hentz traveled to Saleucami to set up Vos' meeting with Sora Bulq, whom he believed to be the second Sith. In a city cantina, she met Skorr and a few Anzati who were warned about her. Skorr told her to relay to Vos that he is allowed inside the base. He then called her a little bug and intimidated her by Force choking her. After having his little fun, Skorr told Hentz that Vos didn't love her—he used her. While gasping for breath, Hentz murmured behind his back that Vos loved her.

Hentz then came back to the Republic base, trying to make "a toy" work until Quinlan came in and told her that it was a holocron. She told him the plan and then spent a night with him.

Hentz was then captured by Skorr, who brought her to show Vos the truth of her mission. Hentz confessed that she was Dooku's double agent and pretended to love him but then fell in love with him for real. She pleaded with her love to look at her to see the truth. Despite urgings from Dooku and Bulq to kill her in order to complete his transition to the dark side, Vos cupped Hentz's face in his hands, kissed her and then ignited his lightsaber to free her of her cuffs. But with Dark Jedi and Anzati surrounding them, escape seemed impossible, until Tholme showed up. While the Jedi battled against their dark counterparts, Hentz killed every Anzati that tried to take her "soup". But when Quinlan fought against Sora Bulq and was getting closer to the dark side, Secura and Tholme joined to save him; Hentz thought that he was dying. When Vos killed Bulq, they managed to escape the base when the Republic began bombardment. Soon, Vos learned another secret Hentz was hiding—she was pregnant with his child. He decided that when the war was over, he would leave the Jedi Order to be with her. He told her to take the Skorp-Ion to a safe place in the galaxy.

Jan Duursema stated the following about Quinlan and Khaleen's marriage:

"The Kiffar version of marriage is not a ceremony or a legal document. Kiffar 'marriage' is more of a state of mind or a state of being. Through Korto, Khaleen and Quin have an unbreakable connection--and a responsibility that transcends their own separate lives. If you create life, you nurture that life, whatever hardships lie ahead."[6]